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30th August 2013 @ 13:31

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Reaction information

*#Reaction file
*Reaction file type CDX

n-Butyllithium (4.2 mL of a 2.5 M solution in hexanes, 10.5 mmol) is added dropwise to a solution of 5-(1, 2-Dichloro-1-ethenyl)oxy)-1-pentene (835 mg, 5 mmol) in THF (8 mL) at –78 °C (internal thermometer) under Ar. After 30 minutes at below –70 °C, the solution is allowed to warm to –40 °C over 30 minutes. The appropriate iodide (5 mmol) in HMPA (2 mL) is added, and the resultant orange solution stirred to room temperature for 4 h. MeOH (3 mL) is added to the dark red solution, and the mixture poured into cold saturated NH4Cl solution (20 mL) and pentane (20 mL). The aqueous layer is separated, and extracted into pentane (3 x 20 mL). The combined organic phases are washed with water then brine, dried over Na2SO4, filtered and concentrated, to give a brown oil. The crude product is purified by column chromatography (neutral alumina, petrol) to give 1-(4-Pentenyloxy)-1-heptyne a clear, pale yellow oil (534 mg, 60%).

*Yield (%) 60
*Type of Yield Isolated Product Yield
Further information Compound 202: 1-(4-Pentenyloxy)-1-heptyne

For multistep reactions (or their steps):

Overall reaction? False 
For overall reaction - links to child reaction steps N/A 
For step in multistep reaction - link to previous reaction step Reaction 201 
For step in multistep reaction - link to following reaction step Reaction 203
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